How to Convince Your Boss to Let You Work from Home

More and more people are working remotely, and many say it improves their productivity and satisfaction — while also saving them time and money. If you’re commuting to an office every day but would like to work elsewhere on a weekly basis, how can you convince your boss to let you do so? What arguments or evidence should you use? And what factors will increase your chances of securing a regular work-at-home schedule?

What the Experts SayThe 9-to-5, Monday-to-Friday schedule has its “origins in the Industrial Revolution,” says Nicholas Bloom, a Stanford University professor. “But times, they are a-changin’. We live in a different era.” Still, working from home has a bad rap. “Some people are deeply skeptical about it,” he says. “They refer to it as ‘shirking from home’ or ‘working remotely, remotely working. They think it means goofing off and watching cartoons.” But, in fact, research suggests the opposite: Working from home increases productivity, efficiency, and engagement. “It is possible to be as, or more, productive” at home as in the office, says Karen Dillon, coauthor of several best-selling titles, including How Will You Measure Your Life? Not only does working from home eliminate your commute, which for most people is “total wasted time,” but it also “allows you to be more focused and efficient.” Of course, “you’re only going to get this opportunity if you’re already valued and trusted,” Dillon says. So be sure you’re in good standing with your manager before making the request. Here are some strategies to convince your boss to let you work remotely.

Reflect on your motivationsBefore broaching the subject with your boss, be clear on why you wish to work from home in the first place. Perhaps your motivation is purely professional. Back-to-back meetings, a constant stream of conference calls, and obligatory break room chitchat make it next to impossible to complete important tasks. Working remotely, on the other hand, “gives you the time and space to concentrate without distractions,” Bloom says. Or maybe your reasons are personal, Dillon adds. You’re feeling “the tugs of your life,” whether they’re child care responsibilities, fitness goals, or caring for aging parents, encroaching on your time and sanity. Working from home on a regular basis could “change the dynamics of your week.” Whatever your motives, you need “to be honest with yourself about what you’re asking for” and make sure your intentions are pure, she says. It would be unfair to “do a bait and switch” with your boss “by saying you want to work from home to be more productive, but really it’s that you want to be at home with your child and check email only occasionally.”

Devise a planNext, Dillon says, you need to consider what a realistic remote work schedule would look like. What do you want? Is it to work Tuesdays and Thursdays from home? Every other Friday? Or would flex hours suffice? And try to “imagine how your boss will hear your proposal.” Consider what will worry your manager, and then think of ways to preempt those concerns. For instance, you might need to have a backup plan for flexibility. “There should be no absolutes,” Dillon says. “Your boss needs to know you can make it to an important Friday meeting, even if that’s your work-from-home day.” You should also strategize about how you’ll manage “the optics” of working from home in terms of “being present on email and available by phone,” she says. “Your manager needs for other people to not see your schedule as a four-day week.” A tip: If you’re proposing to work from home a single day per week, try for Wednesday. This way, your boss won’t perceive your request as a means to elongate your weekends, Bloom says. “Wednesday is not a slacker day,” he says. “It’s the middle of the week, and it’s a day for concentrated work, like detailed analysis.”

Talk to your bossYour proposal should be simple and straightforward, Dillon says. Explain to your boss, “Here’s what I am thinking, here’s why, and here’s what the organization will gain.” That last point is critical. “Don’t steamroll your boss with research, but there’s no harm in using empirical evidence” to make your case more compelling. You might say, for instance, “I read an interesting article in HBR that shows how allowing employees to work from home improves results.” After all, “it’s hard to argue with someone who is reasoned, reasonable, and prepared.” Even though it’s effective to frame your argument in terms of the benefits to your company, the personal gains derived from working from home, that fact that you’ll be less stressed and therefore happier in your job, are also worth highlighting, Bloom says. “Many managers understand that people find working from home valuable and motivating,” he says. It’s a “cost-effective way to retain” your best people.

Give your boss timeAs much as you’d like to leave your manager’s office having made the sale, it’s important “not to push for a yes or no right away,” Dillon says. If your initial conversation goes well, “present your boss with a one-page proposal — nothing elaborate — that details your plan.” And then back off. “Your manager needs time to think about the implications, or maybe get approval from HR. “Give them the time and space to do that.” Take solace in the fact that if you’ve made a convincing argument, “your boss will not want to lose a good employee.”

Be willing to experimentOne way to get your boss to warm to a regular work-from-home schedule is to suggest a three- or six-month trial period, Bloom says. “A pilot is a low-risk way to see whether an arrangement like this can work,” he says. “Ask your boss if you can roll it out for a few months; if it doesn’t work, you can roll it back.” If your manager agrees to the plan, Dillon suggests “overcommunicating in the beginning” and “presenting your boss with a list of what you accomplished last week and your to-do list for the coming one.” After the trial ends, she recommends having “a calibration conversation” to discuss whether “your mutual expectations were met.”

Push for organizational change“Allowing employees to work from home is increasingly a standard practice” at organizations around the world, Bloom says, but not all companies are so enlightened. If your request is denied, don’t take it personally, Dillon adds. It’s likely that there are “bigger cultural issues” at play; maybe your boss thinks, “If I do it for you, I’m going to have to do it for everybody.” So think of “constructive ways to take no for an answer.” You might talk to HR about implementing a new workplace policy or form a small group of colleagues “to investigate how other organizations handle this.” The goal is to “remove the burden of making the decision” from one single manager.

Just do itThere is an argument for “just taking the plunge” into remote working without explicitly asking for permission, Bloom says. “Luck rewards the brave.” The next time an opportunity presents itself — a bad snowstorm, a disruptive event (such as your city hosting a large sporting event or convention), or even a planned home visit from your local cable company — “seize the day” and be as “effective as possible” in your remote work. Demonstrating that you can be productive is “a successful backdoor strategy” to getting your manager to sign off on a permanent arrangement, Dillon says. “It proves that you can manage it.” Don’t be sneaky, though. “You don’t want your boss to think you’re abusing their good will.”

Principles to Remember

Do:

Be honest with yourself about your motivations for wanting to work from home

Make your case with empirical evidence. It’s hard to argue with someone who is reasonable and prepared

Experiment with a three- or six-month test run, after which you and your boss discuss what went well and what needs fine-tuning

Don’t:

Bother with an elaborate presentation of your argument; a conversation followed up with a one-page proposal is appropriate

Be deterred if your request isn’t granted. Form a group of colleagues to investigate how other organizations handle employees working from home, and present your findings to HR

Be sneaky. Take advantage of opportunities to demonstrate that you can work from home effectively and productively

Case Study #1: Propose a pilot and then ace it by being responsive and productiveTwo years ago, when Mark Scott took the job as chief marketing officer at Apixio, a digitized medical records company, he knew that his commute would be bad. “But I didn’t realize quite how brutal it would be,” he says.

The 40-mile commute from his home in the East Bay to his office in San Mateo typically takes about an hour and a half — each way.

After about six months at the company, this “wasted productivity” was getting to him. In a previous job he’d worked from home four days a week, and he knew he needed to ask his current boss if he could do something similar in the new role.

While Apixio didn’t have a formal policy on working from home, Mark was confident that the company’s culture was “open, supportive, and adaptable” and that his boss would sympathize with him. But he also knew that he would need to “quell any concerns” about him not being physically present. “I lead the marketing team, and I am on the executive team,” he says. “Face time in the office is important.”

Mark suggested a pilot that involved him working from home every Tuesday. “Our staff meetings are on Mondays, so Tuesdays made a lot of sense,” he says. “I told my boss I’d like to try it out for a few months and see how it goes.”

He added that he would, of course, come in on any Tuesday he was needed. “I wanted him to know that I was committed to the team and that I would be flexible.”

His boss agreed to the trial. All Mark had to do was “kill it” as a remote worker. “The best way to get traction is to demonstrate that you are accessible, productive, and responsive. The proof is in the pudding.”

The new arrangement was indeed successful, and Mark continues to work from home regularly, with support from his boss. “We never had a formal conversation about it, because it was going so well,” he says. “He said, ‘Just work from home when you need to. It’s fine.’”

Mark encourages his team members to work remotely on projects that require intense concentration. “Now even our CEO and CFO work from home from time to time,” he says. “Sometimes you just need a break from the water cooler chat.”

Case Study #2: Present evidence to make your case, and then be flexible and committed to the jobWade Vielock had worked as a manager at Employer Flexible, a Houston-based human resources and recruitment company, for a year before he was transferred to San Antonio. At the time, the company had only a modest presence there, and Wade’s business agenda included making hires and building out the sales and service teams.

Two years later Wade earned a promotion, and his boss asked him to come back to corporate headquarters. But returning to Houston was not something Wade was prepared to do. “I have a wife and two kids, and I really didn’t want to pick up and move back” so soon, he says.

So he devised a plan. Wade would continue to live and work in San Antonio, both at the company’s office and at home, but he would spend three days in Houston every other week. He would also make himself available for special meetings at headquarters, even on short notice. “I realized that it’s a sacrifice for the company, so I have to be flexible,” he says.

To build his case to his boss, Wade used internal examples of successful remote workers. For instance, he pointed to his own direct reports, who often spent days at home when they need “heads down” time to write surveys or handbooks, and were getting high marks from clients as a result.

Wade’s boss agreed to a yearlong trial. “He said, ‘Let’s see how the role develops and reevaluate.’”

Wade stayed on schedule. When he was at headquarters, he often worked 12-hour days and made sure to have lots of one-on-one meetings with his team. When he was working remotely, he made sure he was “overly accessible.”

“I wanted to make sure [my colleagues] would see no difference in my delivery, regardless of whether I was sitting at my desk in Houston or my desk in San Antonio,” he says. “When you work remotely, you have to produce at 110%.”

After the year was up, Wade received a positive performance review. “My boss said, ‘You’re hitting your numbers and the [remote work situation] is a nonissue.’” Wade was even told that he might not need to commute every other week and could cut it down to every three weeks instead. But he hasn’t made that switch yet. “I like the face time with my team,” he explains.

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